WO2000002546A2 - Methode de traitement de l'insomnie - Google Patents

Methode de traitement de l'insomnie Download PDF

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Publication number
WO2000002546A2
WO2000002546A2 PCT/US1999/015058 US9915058W WO0002546A2 WO 2000002546 A2 WO2000002546 A2 WO 2000002546A2 US 9915058 W US9915058 W US 9915058W WO 0002546 A2 WO0002546 A2 WO 0002546A2
Authority
WO
WIPO (PCT)
Prior art keywords
formula
gabapentin
hydrogen
insomnia
compounds
Prior art date
Application number
PCT/US1999/015058
Other languages
English (en)
Other versions
WO2000002546A3 (fr
Inventor
Leslie Magnus-Miller
Catherine A. Segal
Original Assignee
Warner-Lambert Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to AU49673/99A priority Critical patent/AU765038B2/en
Priority to JP2000558806A priority patent/JP2002520277A/ja
Priority to NZ509231A priority patent/NZ509231A/en
Priority to PL99345338A priority patent/PL345338A1/xx
Priority to CA002333024A priority patent/CA2333024C/fr
Priority to EP99933667A priority patent/EP1094803A2/fr
Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company
Priority to KR1020017000261A priority patent/KR20010071778A/ko
Priority to BR9911887-4A priority patent/BR9911887A/pt
Priority to US09/743,370 priority patent/US6306910B1/en
Publication of WO2000002546A2 publication Critical patent/WO2000002546A2/fr
Publication of WO2000002546A3 publication Critical patent/WO2000002546A3/fr
Priority to NO20010117A priority patent/NO20010117D0/no

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives

Definitions

  • the present invention relates to the use of analogs of glutamic acid and gamma-aminobutyric acid (GAB A) for the treatment of insomnia.
  • GAB A gamma-aminobutyric acid
  • GABA analogs are known agents useful in antiseizure therapy for central nervous system disorders such as epilepsy, Huntington's chorea, cerebral ischemia. Parkinson's disease, tardive dyskinesia, and spasticity. It has also been suggested that the compounds can be used as antidepressants, anxiolytics, and antipsychotics. See WO 92/09560 (United States Serial Number 618,692 filed November 27, 1990) and WP 93/23383 (United States Serial Number 886.080 filed May 20, 1992).
  • WO 97/33858 teaches that compounds related to gabapentin are useful or treating epilespy. faintness attacks, hypokinesia. cranial disorders, neurodegenerative disorders, depression, anxiet ⁇ . panic, pain, and neuropathological disorders. WO 97/33858 does not specify what forms of pain are treated.
  • the compounds of the invention are known for treatment of neuropathic pain.
  • Ann Pharmacother 1997 Sep, 31:9, 1082-3; Zapp JJ., Postpoliomyelitis pain treated with gabapentin [letter].
  • insomnia and sleeplessness are common problems. Often, the insomnia or sleeplessness is precipitated by stress, emotional and physical causes.
  • U.S. Patent No. 5,510,381 directed to the use of gabapentin to treat mania, mentions one study in which gabapentin has also been found to enhance delta- wave (deep) sleep. This effect is beneficial in acute mania and also leads to reducing the risk for onset of a new episode of mania.
  • This invention provides a method for treating insomnia in a mammal comprising administering to a subject suffering from insomnia an effective amount of a GABA analog.
  • a preferred embodiment utilizes a cyclic amino acid compound of Formula I
  • R ⁇ is hydrogen or lower alkyl and n is an integer of from 4 to 6, and the pharmaceutically acceptable salts thereof.
  • An especially preferred embodiment utilizes a compound of Formula I where R ⁇ is hydrogen and n is 4, which compound is 1 -(aminomethyl)-cyclohexane acetic acid, known genetically as gabapentin.
  • the invention includes treating insomnia with a compound of Formula II.
  • R2 is a straight or branched alkyl of from 1 to 6 carbon atoms, phenyl, or cycloalkyl having from 3 to 6 carbon atoms;
  • R 3 is hydrogen or methyl; and ( is hydrogen, methyl, or carboxyl; or an individual enantiomeric isomer thereof; or a pharmaceutically acceptable salt thereof, in unit dosage form, to a mammal in need of said treatment.
  • Preferred compounds of the invention are those wherein R4 and R3 are hydrogen, and R2 is -(CH2) ⁇ -2"i C4H9 as an (R), (S), or (R,S) isomer.
  • the method of this invention utilizes any GABA analog.
  • a GABA analog is any compound derived from or based upon gamma-aminobutyric acid.
  • the compounds are readily available, either commercially, or by synthetic methodology well-known to those skilled in the art of organic chemistry.
  • the preferred GABA analogs to be utilized in the method of this invention are cyclic amino acids of Formula I. These are described in U.S. Patent 4,024,175, which is incorporated herein by reference.
  • Another preferred method utilizes the GABA analogs of Formula II, and these are described in U.S. Patent 5,563,175 which is incorporated herein by reference.
  • All that is required to practice the method of this invention is to administer a GABA analog in an amount that is effective to treat insomnia.
  • Such amounts will generally be from about 1 to about 300 mg per kg of subject body weight.
  • Typical doses will be from about 10 to about 5000 mg per day for an adult subject of normal weight. It is expected that common doses that might be administered could be from 100 mg three times a day up to 600 mg four times a day.
  • Commercially available capsules of 100 mg, 300 mg, and 400 mg of gabapentin can be administered.
  • Alternate forms include liquids and film-coated tablets.
  • the dosage level is one sixth that of gabapentin.
  • the dosage range for pregabalin is from about 0.15 mg to about 50 mg per kg per day of subject body weight. Typical dosages for pregabalin will be from about 1.6 mg to about 840 mg per day with individual dosages ranging from abut 0.15 mg to about 65 mg per dose.
  • the compounds used in the present invention may form pharmaceutically acceptable salts with both organic and inorganic acids or bases.
  • the acid addition salts of the basic compounds are prepared either by dissolving the free base in aqueous or aqueous alcohol solution or other suitable solvents containing the appropriate acid and isolating the salt by evaporating the solution.
  • pharmaceutically acceptable salts are hydrochlorides, hydrobromides, hydrosulfates, etc. as well as sodium, potassium, and magnesium, etc. salts.
  • the compounds of the Formula II can contain one or several asymmetric carbon atoms.
  • the invention includes the individual diastereomers or enantiomers, and the mixtures thereof.
  • the individual diastereomers or enantiomers may be prepared or isolated by methods already well-known in the art.
  • compositions of the compound of the present invention or its salts are produced by formulating the active compound in dosage unit form with a pharmaceutical carrier.
  • dosage unit forms are tablets, capsules, pills, powders, aqueous and nonaqueous oral solutions and suspensions, and parenteral solutions packaged in containers containing either one or some larger number of dosage units and capable of being subdivided into individual doses.
  • suitable pharmaceutical carriers including pharmaceutical diluents
  • suitable pharmaceutical carriers are gelatin capsules; sugars such as lactose and sucrose; starches such as corn starch and potato starch, cellulose derivatives such as sodium carboxymethyl cellulose, ethyl cellulose, methyl cellulose, and cellulose acetate phthalate; gelatin; talc; stearic acid; magnesium stearate; vegetable oils such as peanut oil, cottonseed oil, sesame oil, olive oil, corn oil, and oil of theobroma; propylene glycol, glycerin; sorbitol; polyethylene glycol; water; agar; alginic acid; isotonic saline, and phosphate buffer solutions; as well as other compatible substances normally used in pharmaceutical formulations.
  • the compositions of the invention can also contain other components such as coloring agents, flavoring agents, and or preservatives. These materials, if present, are usually used in relatively small amounts.
  • the compositions can, if desired, also contain
  • the percentage of the active ingredients in the foregoing compositions can be varied within wide limits, but for practical purposes it is preferably present in a concentration of at least 10% in a solid composition and at least 2% in a primary liquid composition.
  • the most satisfactory compositions are those in which a much higher proportion of the active ingredient is present.
  • a useful intravenous dose is between 5 and 50 mg and a useful oral dosage is between 20 and 800 mg.
  • the dosage is within the dosing range used in treatment of pain or as would be with the needs of the patient as described by the physician.
  • GABA analogs to treat insomnia are not addictive. Additionally, GABA analogs have a half-life in the body that is suitable to work during the evening and subsequently clear the body by morning to allow for easy arousal. GAGA analog's, particularly gabapentin' s, method of action is different from other sleep enchancing agents.
  • the GABA analogs can be combined with other agents to enhance the sleep inducing effects. Such agents include melatonin, trytophan, valerian, passiflora, antihistamines, such as diphenydramine hydrochloride or doxylamine succinate, densokiazepene and non- benzodipend hypnotics.
  • Additional advantages of using the compounds of Formula I and II, especially gabapentin and pregabalin, in the present invention include the relatively nontoxic nature of the compounds, the ease of preparation, the fact that the compounds are well-tolerated, and the ease of IV administration of the drugs.
  • Gabapentin has few interactions with major classes of drugs since it is not metabolized in the liver, but rather excreted unchanged from the body. Further, the drugs are not metabolized in the body.
  • the subjects treated with the method of the present invention are mammals, including humans.
  • the GABA analogs used in the method of the present invention are not addictive. This is a significant advantage over other sleep aids. Also, these compounds have a half life that is suitable to work during the evening and subsequently clear the body by morning to allow for easy arousal.
  • the method of action of the GABA analogs is different than other hypnotics and thus can be combined with them to enhance the sleep inducing effects.
  • These agents could include melatonin, trytophan, valerian, passiflora, classical antihistamines such as diphenhydramine hydrochloride or doxylamine succinate, as well as benzodiazepene and non-benzodiazepene hypnotics.

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  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Neurosurgery (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pain & Pain Management (AREA)
  • Anesthesiology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention porte sur un procédé de traitement de l'insomnie utilisant certains analogues de l'acide glutamique et de l'acide gamma-aminobutyrique.
PCT/US1999/015058 1998-07-09 1999-07-01 Methode de traitement de l'insomnie WO2000002546A2 (fr)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2000558806A JP2002520277A (ja) 1998-07-09 1999-07-01 不眠症を治療する方法
NZ509231A NZ509231A (en) 1998-07-09 1999-07-01 Use of GABA analogs to treat insomnia
PL99345338A PL345338A1 (en) 1998-07-09 1999-07-01 Method for the treatment of insomnia
CA002333024A CA2333024C (fr) 1998-07-09 1999-07-01 Methode de traitement de l'insomnie
EP99933667A EP1094803A2 (fr) 1998-07-09 1999-07-01 Methode de traitement de l'insomnie
AU49673/99A AU765038B2 (en) 1998-07-09 1999-07-01 Method for the treatment of insomnia
KR1020017000261A KR20010071778A (ko) 1998-07-09 1999-07-01 불면증의 치료를 위한 ｇａｂａ 유사체의 용도
BR9911887-4A BR9911887A (pt) 1998-07-09 1999-07-01 Método para o tratamento da insÈnia
US09/743,370 US6306910B1 (en) 1998-07-09 1999-07-01 Use of Gaba-analogues for treating insomnia
NO20010117A NO20010117D0 (no) 1998-07-09 2001-01-08 Fremgangsmåte for behandling av sövnlöshet

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9216698P 1998-07-09 1998-07-09
US60/092,166 1998-07-09

Publications (2)

Publication Number Publication Date
WO2000002546A2 true WO2000002546A2 (fr) 2000-01-20
WO2000002546A3 WO2000002546A3 (fr) 2000-06-15

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/015058 WO2000002546A2 (fr) 1998-07-09 1999-07-01 Methode de traitement de l'insomnie

Country Status (13)

Country Link
US (2) US6306910B1 (fr)
EP (1) EP1094803A2 (fr)
JP (1) JP2002520277A (fr)
KR (1) KR20010071778A (fr)
AU (1) AU765038B2 (fr)
BR (1) BR9911887A (fr)
CA (1) CA2333024C (fr)
ID (1) ID27191A (fr)
NO (1) NO20010117D0 (fr)
NZ (1) NZ509231A (fr)
PL (1) PL345338A1 (fr)
WO (1) WO2000002546A2 (fr)
ZA (1) ZA200007174B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000209A2 (fr) * 2000-06-26 2002-01-03 Warner-Lambert Company Analogues de gabapentine pour traiter les troubles du sommeil
WO2004054565A1 (fr) * 2002-12-13 2004-07-01 Warner-Lambert Company Llc Pregabalin et derives de pregabalin pour le traitement de la fibromyalgie et d'autres troubles connexes
AU2005292853B2 (en) * 2004-10-14 2009-08-20 Daikin Industries, Ltd. Atmosphere modifying method and spray agent and spray device used in the same

Families Citing this family (23)

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US6001876A (en) 1996-07-24 1999-12-14 Warner-Lambert Company Isobutylgaba and its derivatives for the treatment of pain
US6992109B1 (en) * 1999-04-08 2006-01-31 Segal Catherine A Method for the treatment of incontinence
US7164034B2 (en) * 1999-06-10 2007-01-16 Pfizer Inc. Alpha2delta ligands for fibromyalgia and other disorders
US20080207755A1 (en) * 2000-05-31 2008-08-28 Pfizer Inc Alpha 2 Delta Ligands For Fibromyalgia and Other Disorders
US7186855B2 (en) 2001-06-11 2007-03-06 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en) 2005-04-06 2011-11-01 Xenoport, Inc. Prodrugs of GABA analogs, compositions and uses thereof
US20030225149A1 (en) * 2002-04-30 2003-12-04 Blazecka Peter G. Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids
US7071339B2 (en) * 2002-08-29 2006-07-04 Warner Lambert Company Llc Process for preparing functionalized γ-butyrolactones from mucohalic acid
US7025745B2 (en) * 2002-10-07 2006-04-11 Advanced Cardiovascular Systems, Inc. Method of making a catheter balloon using a tapered mandrel
CA2451267A1 (fr) * 2002-12-13 2004-06-13 Warner-Lambert Company Llc Utilisations pharmaceutiques de ligands alpha2delta
JP2006513257A (ja) 2002-12-13 2006-04-20 ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー 線維筋痛症および他の障害を処置するためのプレガバリン誘導体
NZ540336A (en) * 2002-12-13 2008-03-28 Warner Lambert Co Gabapentin analogues for fibromyalgia and other related disorders
DK1727620T3 (da) * 2004-03-12 2007-12-03 Warner Lambert Co C1 symmetriske biphosphinlegander og deres anvendelse i asymmetrisk syntese af pregabilin
JP4504063B2 (ja) * 2004-03-30 2010-07-14 エスエス製薬株式会社 睡眠改善薬
CA2561755A1 (fr) * 2004-04-01 2005-10-13 Warner-Lambert Company Llc Preparation de phospholanes p-chirogenes et utilisation de ceux-ci dans une synthese asymetrique
JP4613031B2 (ja) * 2004-05-06 2011-01-12 エスエス製薬株式会社 催眠剤組成物
EA015418B1 (ru) * 2004-06-21 2011-08-30 УОРНЕР-ЛАМБЕРТ КОМПАНИ ЭлЭлСи Получение прегабалина и родственных соединений
KR100606103B1 (ko) * 2005-07-15 2006-07-31 삼성전자주식회사 서로 다른 통신망 간의 ｐｓ호의 핸드오버 방법 및 이를 위한 듀얼모드 단말기
EP2101752A1 (fr) * 2006-12-08 2009-09-23 Xenoport, Inc. Utilisation de promédicaments à base d'analogues de gaba pour le traitement de certaines maladies
EP2285365A1 (fr) * 2007-08-03 2011-02-23 Tullin, Søren Utilisation d'une composition contenant au moins un bêta-bloquant pour le traitement de troubles du sommeil
SG176464A1 (en) 2008-05-09 2011-12-29 Agency Science Tech & Res Diagnosis and treatment of kawasaki disease
WO2011141923A2 (fr) 2010-05-14 2011-11-17 Lupin Limited Synthèse améliorée d'un ester alkylique optiquement pur de l'acide (s) - 3-cyano-5-méthyl-hexanoïque, intermédiaire de la (s)-prégabaline
WO2012059797A1 (fr) 2010-11-04 2012-05-10 Lupin Limited Procédé de synthèse de la (s)-prégabaline

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002000209A2 (fr) * 2000-06-26 2002-01-03 Warner-Lambert Company Analogues de gabapentine pour traiter les troubles du sommeil
WO2002000209A3 (fr) * 2000-06-26 2003-01-16 Warner Lambert Co Analogues de gabapentine pour traiter les troubles du sommeil
US7141606B2 (en) 2000-06-26 2006-11-28 Warner-Lambert Company Gabapentin analogues for sleep disorders
KR100785182B1 (ko) * 2000-06-26 2007-12-11 워너-램버트 캄파니 엘엘씨 수면 장애를 위한 가바펜틴 유사체
WO2004054565A1 (fr) * 2002-12-13 2004-07-01 Warner-Lambert Company Llc Pregabalin et derives de pregabalin pour le traitement de la fibromyalgie et d'autres troubles connexes
AU2005292853B2 (en) * 2004-10-14 2009-08-20 Daikin Industries, Ltd. Atmosphere modifying method and spray agent and spray device used in the same
AU2005292853C1 (en) * 2004-10-14 2010-08-05 Daikin Industries, Ltd. Atmosphere modifying method and spray agent and spray device used in the same

Also Published As

Publication number Publication date
CA2333024C (fr) 2002-03-26
US6306910B1 (en) 2001-10-23
NZ509231A (en) 2003-08-29
ZA200007174B (en) 2002-03-04
CA2333024A1 (fr) 2000-01-20
NO20010117L (no) 2001-01-08
JP2002520277A (ja) 2002-07-09
NO20010117D0 (no) 2001-01-08
WO2000002546A3 (fr) 2000-06-15
ID27191A (id) 2001-03-08
PL345338A1 (en) 2001-12-17
EP1094803A2 (fr) 2001-05-02
KR20010071778A (ko) 2001-07-31
AU4967399A (en) 2000-02-01
AU765038B2 (en) 2003-09-04
US20020004528A1 (en) 2002-01-10
BR9911887A (pt) 2001-03-27

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